Eastern white pine (Pinus strobus) is considered a signature species in eastern North America, particularly in New England. In recent years, however, white pine has experienced increased damage due to native pathogens that reduce the species’ growth, productivity, and economic value. One disease of concern is Caliciopsis canker, caused by the fungal pathogen Caliciopsis pinea, which is associated with excessive resin production, cankers, rough bark, bark fissures/cracks, and reduced growth in white pine. Recent studies have documented the extent of Caliciopsis canker in New England and its association with soil and stocking conditions, yet few studies have focused on the biological impacts of the disease. This study used dendrochronology and whole-tree dissections to reconstruct Caliciopsis canker history in three New England white pine sites, quantify its impact on tree growth and vigor, identify pre-disposing factors, and assess potential silvicultural management options. Dendrochronology and whole-tree dissections provided a unique insight into canker damage throughout trees’ development. Canker damage was first reported in New Hampshire in the mid-1990s, yet cankers were present as far back as 1967 and have steadily increased since the mid-1980s. Increased canker damage was significantly associated with decreased live crown ratios and declining tree growth. Trees maintaining a 30% live crown ratio or greater generally experienced the least canker damage. Furthermore, peaks in canker occurrence were consistent across sites, indicating a regional synchronization of infection and damage. Canker damage was closely associated with climatic events such as droughts and a New England hurricane. The results suggest that Caliciopsis canker has been affecting white pine health over the last 40 years, and that the disease has become more prevalent in the past 20–30 years. Yet, our results suggest that if silvicultural prescriptions target low density thinnings that favor trees with higher live crown ratios (>30%) and low Caliciopsis symptom severity ratings, the risk of canker damage can be reduced in white pine stands.